TW575579B - Process for the recovery of N-phosphonomethylglycine - Google Patents
Process for the recovery of N-phosphonomethylglycine Download PDFInfo
- Publication number
- TW575579B TW575579B TW91113652A TW91113652A TW575579B TW 575579 B TW575579 B TW 575579B TW 91113652 A TW91113652 A TW 91113652A TW 91113652 A TW91113652 A TW 91113652A TW 575579 B TW575579 B TW 575579B
- Authority
- TW
- Taiwan
- Prior art keywords
- phosphonic acid
- mixture
- scope
- methylglycine
- retentate
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 47
- 238000011084 recovery Methods 0.000 title claims description 4
- XDDAORKBJWWYJS-UHFFFAOYSA-N glyphosate Chemical compound OC(=O)CNCP(O)(O)=O XDDAORKBJWWYJS-UHFFFAOYSA-N 0.000 title description 3
- 239000012528 membrane Substances 0.000 claims description 46
- 108010077895 Sarcosine Proteins 0.000 claims description 39
- 239000012465 retentate Substances 0.000 claims description 38
- FSYKKLYZXJSNPZ-UHFFFAOYSA-N sarcosine Chemical compound C[NH2+]CC([O-])=O FSYKKLYZXJSNPZ-UHFFFAOYSA-N 0.000 claims description 38
- 239000000203 mixture Substances 0.000 claims description 35
- 239000012466 permeate Substances 0.000 claims description 27
- 238000000926 separation method Methods 0.000 claims description 23
- 239000012527 feed solution Substances 0.000 claims description 15
- -1 tris (phosphino) phosphite Chemical compound 0.000 claims description 13
- 239000012452 mother liquor Substances 0.000 claims description 11
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 10
- 238000001728 nano-filtration Methods 0.000 claims description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 7
- 239000000047 product Substances 0.000 claims description 6
- 229910001615 alkaline earth metal halide Inorganic materials 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 229910021529 ammonia Inorganic materials 0.000 claims description 5
- 150000004820 halides Chemical class 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 4
- 229910001508 alkali metal halide Inorganic materials 0.000 claims description 4
- 150000001340 alkali metals Chemical class 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 4
- 238000011026 diafiltration Methods 0.000 claims description 4
- 239000012535 impurity Substances 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 239000002585 base Substances 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 238000002955 isolation Methods 0.000 claims description 2
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 claims description 2
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims 2
- 125000001309 chloro group Chemical class Cl* 0.000 claims 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
- KQSSATDQUYCRGS-UHFFFAOYSA-N methyl glycinate Chemical compound COC(=O)CN KQSSATDQUYCRGS-UHFFFAOYSA-N 0.000 claims 1
- 230000000717 retained effect Effects 0.000 claims 1
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 16
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- JWTSJFBZEPJSLQ-UHFFFAOYSA-N CNCC(=O)O.P(O)(O)=O Chemical compound CNCC(=O)O.P(O)(O)=O JWTSJFBZEPJSLQ-UHFFFAOYSA-N 0.000 description 8
- 239000004471 Glycine Substances 0.000 description 8
- 239000000243 solution Substances 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 230000003204 osmotic effect Effects 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- MGRVRXRGTBOSHW-UHFFFAOYSA-N (aminomethyl)phosphonic acid Chemical compound NCP(O)(O)=O MGRVRXRGTBOSHW-UHFFFAOYSA-N 0.000 description 4
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 239000004809 Teflon Substances 0.000 description 4
- 229920006362 Teflon® Polymers 0.000 description 4
- 239000008346 aqueous phase Substances 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 235000019270 ammonium chloride Nutrition 0.000 description 3
- 238000002425 crystallisation Methods 0.000 description 3
- 230000008025 crystallization Effects 0.000 description 3
- 238000010586 diagram Methods 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 230000014759 maintenance of location Effects 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 230000003647 oxidation Effects 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 238000005903 acid hydrolysis reaction Methods 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- WVVMIXKCDPEXKC-UHFFFAOYSA-N carboxymethyl(methyl)azanium dihydrogen phosphate Chemical compound OP(O)([O-])=O.C[NH2+]CC(O)=O WVVMIXKCDPEXKC-UHFFFAOYSA-N 0.000 description 2
- 239000000919 ceramic Substances 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 229910000000 metal hydroxide Inorganic materials 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000001223 reverse osmosis Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 239000002351 wastewater Substances 0.000 description 2
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 1
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- KWIPUXXIFQQMKN-UHFFFAOYSA-N 2-azaniumyl-3-(4-cyanophenyl)propanoate Chemical compound OC(=O)C(N)CC1=CC=C(C#N)C=C1 KWIPUXXIFQQMKN-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 239000005562 Glyphosate Substances 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
- AZIHIQIVLANVKD-UHFFFAOYSA-N N-(phosphonomethyl)iminodiacetic acid Chemical compound OC(=O)CN(CC(O)=O)CP(O)(O)=O AZIHIQIVLANVKD-UHFFFAOYSA-N 0.000 description 1
- CCQCTZALOONOAE-UHFFFAOYSA-N OC(=O)CNP(O)(=O)OP(O)(O)=O Chemical compound OC(=O)CNP(O)(=O)OP(O)(O)=O CCQCTZALOONOAE-UHFFFAOYSA-N 0.000 description 1
- 239000003570 air Substances 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001339 alkali metal compounds Chemical class 0.000 description 1
- 150000001341 alkaline earth metal compounds Chemical class 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 229940090948 ammonium benzoate Drugs 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- UYJXRRSPUVSSMN-UHFFFAOYSA-P ammonium sulfide Chemical compound [NH4+].[NH4+].[S-2] UYJXRRSPUVSSMN-UHFFFAOYSA-P 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000004760 aramid Substances 0.000 description 1
- 229920003235 aromatic polyamide Polymers 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 238000010923 batch production Methods 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- WGQKYBSKWIADBV-UHFFFAOYSA-O benzylaminium Chemical compound [NH3+]CC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-O 0.000 description 1
- WUKWITHWXAAZEY-UHFFFAOYSA-L calcium difluoride Chemical compound [F-].[F-].[Ca+2] WUKWITHWXAAZEY-UHFFFAOYSA-L 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 229910001634 calcium fluoride Inorganic materials 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 230000000711 cancerogenic effect Effects 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 231100000315 carcinogenic Toxicity 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 150000003841 chloride salts Chemical class 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 238000010612 desalination reaction Methods 0.000 description 1
- 238000000502 dialysis Methods 0.000 description 1
- SWRNIYAQKATHDJ-UHFFFAOYSA-N dichloro(dichlorophosphanyl)phosphane Chemical compound ClP(Cl)P(Cl)Cl SWRNIYAQKATHDJ-UHFFFAOYSA-N 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 239000012065 filter cake Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 229940097068 glyphosate Drugs 0.000 description 1
- 230000002363 herbicidal effect Effects 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- XAKRTGZVYPZHCO-UHFFFAOYSA-O hydroxy-methoxy-oxophosphanium Chemical group CO[P+](O)=O XAKRTGZVYPZHCO-UHFFFAOYSA-O 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 238000002386 leaching Methods 0.000 description 1
- 150000004692 metal hydroxides Chemical class 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 229910052750 molybdenum Inorganic materials 0.000 description 1
- 239000011733 molybdenum Substances 0.000 description 1
- OEIJHBUUFURJLI-UHFFFAOYSA-N octane-1,8-diol Chemical compound OCCCCCCCCO OEIJHBUUFURJLI-UHFFFAOYSA-N 0.000 description 1
- 229920000620 organic polymer Polymers 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 238000005325 percolation Methods 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 230000010287 polarization Effects 0.000 description 1
- 229920006254 polymer film Polymers 0.000 description 1
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- DPLVEEXVKBWGHE-UHFFFAOYSA-N potassium sulfide Chemical compound [S-2].[K+].[K+] DPLVEEXVKBWGHE-UHFFFAOYSA-N 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 229910052979 sodium sulfide Inorganic materials 0.000 description 1
- GRVFOGOEDUUMBP-UHFFFAOYSA-N sodium sulfide (anhydrous) Chemical compound [Na+].[Na+].[S-2] GRVFOGOEDUUMBP-UHFFFAOYSA-N 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 238000010025 steaming Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 1
- 238000000108 ultra-filtration Methods 0.000 description 1
- 150000003681 vanadium Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/3804—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)] not used, see subgroups
- C07F9/3808—Acyclic saturated acids which can have further substituents on alkyl
- C07F9/3813—N-Phosphonomethylglycine; Salts or complexes thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Separation Using Semi-Permeable Membranes (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10130136A DE10130136A1 (de) | 2001-06-22 | 2001-06-22 | Verfahren zur Gewinnung von N-Phosphonomethylglycin |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| TW575579B true TW575579B (en) | 2004-02-11 |
Family
ID=7689074
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| TW91113652A TW575579B (en) | 2001-06-22 | 2002-10-18 | Process for the recovery of N-phosphonomethylglycine |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US7071354B2 (de) |
| EP (1) | EP1401846B1 (de) |
| JP (1) | JP3987488B2 (de) |
| KR (1) | KR100859383B1 (de) |
| CN (1) | CN1257909C (de) |
| AR (1) | AR034597A1 (de) |
| AT (1) | ATE284890T1 (de) |
| AU (1) | AU2002321099B2 (de) |
| BR (1) | BR0210569B1 (de) |
| CA (1) | CA2451507C (de) |
| DE (2) | DE10130136A1 (de) |
| DK (1) | DK1401846T3 (de) |
| ES (1) | ES2233846T3 (de) |
| IL (2) | IL159072A0 (de) |
| IN (1) | IN2003CH02042A (de) |
| MX (1) | MX234329B (de) |
| NZ (1) | NZ530049A (de) |
| PT (1) | PT1401846E (de) |
| RU (1) | RU2274641C2 (de) |
| SI (1) | SI1401846T1 (de) |
| TW (1) | TW575579B (de) |
| WO (1) | WO2003000704A2 (de) |
| ZA (1) | ZA200400433B (de) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AR039201A1 (es) * | 2003-03-28 | 2005-02-09 | Atanor S A | Procedimiento para purificar soluciones de glifosato mediante nanofiltracion |
| TW200538459A (en) * | 2004-05-21 | 2005-12-01 | Dow Agrosciences Llc | Purification of n-(phosphonomethyl)glycine |
| EP1886976A1 (de) * | 2006-08-09 | 2008-02-13 | Thermphos Trading GmbH | Methode zur Verhinderung der Ablagerungen |
| US7771494B2 (en) * | 2007-01-31 | 2010-08-10 | Monsanto Technology Llc | Process for selective removal of water and impurities from N-(phosphonomethyl)glycine |
| EP2082991A1 (de) | 2008-01-22 | 2009-07-29 | Thermphos Trading GmbH | Verfahren zur Wasseraufbereitung |
| EP2090646A1 (de) | 2008-01-22 | 2009-08-19 | Thermphos Trading GmbH | Oberflächenbehandlungszusammensetzung mit Phosphonsäureverbindungen |
| WO2010135141A1 (en) * | 2009-05-18 | 2010-11-25 | Monsanto Technology Llc | Recovery of phosphorus values and salt impurities from aqueous waste streams |
| KR200453576Y1 (ko) * | 2011-03-14 | 2011-05-17 | 이상호 | 라이트 박스 |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3950402A (en) * | 1972-05-31 | 1976-04-13 | Monsanto Company | Process for producing N-phosphonomethyl glycine |
| US3969398A (en) * | 1974-05-01 | 1976-07-13 | Monsanto Company | Process for producing N-phosphonomethyl glycine |
| RO65811A (fr) | 1974-06-26 | 1979-07-15 | Budapesti Vegyimuevek | Procede pour obtenir du n-phosphonombethyl-glycine |
| HU184601B (en) * | 1979-07-09 | 1984-09-28 | Alkaloida Vegyeszeti Gyar | Process for producing n-/phosphono-methyl/-glycine |
| PL159424B1 (pl) * | 1989-04-18 | 1992-12-31 | Sposób wytwarzania N-fosfonometyloglicyny PL | |
| EP0806428B1 (de) | 1994-11-09 | 2003-01-29 | Showa Denko Kabushiki Kaisha | Verfahren zur Abtrennung von N-Phosphonomethylglycin |
| US5587083A (en) | 1995-04-17 | 1996-12-24 | Chemetics International Company Ltd. | Nanofiltration of concentrated aqueous salt solutions |
| IT1281094B1 (it) * | 1995-12-21 | 1998-02-11 | Graziello Donadello | Procedimento per la produzione di n-fosfonometilglicina e/o suoi sali |
| AR027024A1 (es) | 1999-12-23 | 2003-03-12 | Basf Ag | Procedimiento para la preparacion de n-fosfonometilglicina |
| AR029508A1 (es) | 2000-04-14 | 2003-07-02 | Dow Agrosciences Llc | Proceso para remover y recuperar cloruro de sodio de los efluentes de desecho provenientes de los procesos de fabricacion del acido n-fosfometiliminodiacetico (pmida) |
-
2001
- 2001-06-22 DE DE10130136A patent/DE10130136A1/de not_active Withdrawn
-
2002
- 2002-06-19 AR ARP020102292A patent/AR034597A1/es active IP Right Grant
- 2002-06-21 SI SI200230059T patent/SI1401846T1/xx unknown
- 2002-06-21 MX MXPA03011229 patent/MX234329B/es active IP Right Grant
- 2002-06-21 AT AT02754734T patent/ATE284890T1/de active
- 2002-06-21 NZ NZ530049A patent/NZ530049A/en not_active IP Right Cessation
- 2002-06-21 JP JP2003507107A patent/JP3987488B2/ja not_active Expired - Fee Related
- 2002-06-21 PT PT02754734T patent/PT1401846E/pt unknown
- 2002-06-21 DK DK02754734T patent/DK1401846T3/da active
- 2002-06-21 BR BRPI0210569-1B1A patent/BR0210569B1/pt not_active IP Right Cessation
- 2002-06-21 ES ES02754734T patent/ES2233846T3/es not_active Expired - Lifetime
- 2002-06-21 AU AU2002321099A patent/AU2002321099B2/en not_active Ceased
- 2002-06-21 CN CNB028122143A patent/CN1257909C/zh not_active Expired - Fee Related
- 2002-06-21 RU RU2004101770/04A patent/RU2274641C2/ru not_active IP Right Cessation
- 2002-06-21 US US10/481,565 patent/US7071354B2/en not_active Expired - Fee Related
- 2002-06-21 DE DE50201799T patent/DE50201799D1/de not_active Expired - Lifetime
- 2002-06-21 WO PCT/EP2002/006903 patent/WO2003000704A2/de active IP Right Grant
- 2002-06-21 KR KR1020037016619A patent/KR100859383B1/ko not_active IP Right Cessation
- 2002-06-21 CA CA2451507A patent/CA2451507C/en not_active Expired - Fee Related
- 2002-06-21 IL IL15907202A patent/IL159072A0/xx unknown
- 2002-06-21 EP EP02754734A patent/EP1401846B1/de not_active Expired - Lifetime
- 2002-10-18 TW TW91113652A patent/TW575579B/zh not_active IP Right Cessation
-
2003
- 2003-11-26 IL IL159072A patent/IL159072A/en not_active IP Right Cessation
- 2003-12-03 IN IN2042CH2003 patent/IN2003CH02042A/en unknown
-
2004
- 2004-01-21 ZA ZA200400433A patent/ZA200400433B/en unknown
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US9394173B2 (en) | Recovery of phosphorus values and salt impurities from aqueous waste streams | |
| TW575579B (en) | Process for the recovery of N-phosphonomethylglycine | |
| JP4055210B2 (ja) | アリールシアネートの製造方法 | |
| CN106967124B (zh) | 磷铂化合物的合成和提纯方法及其用途 | |
| JPH07110764B2 (ja) | アルカリ金属次亜リン酸塩の製造方法 | |
| EP1756127B1 (de) | Aufreinigung von n-(phosphonomethyl)glycin | |
| EP0233229B1 (de) | Herstellung von einem allylamin und quaternären diallylammoniumverbindungen | |
| EP2114966A1 (de) | Verfahren zur selektiven entfernung von wasser und unreinheiten aus n-(phosphonmethyl)-glycin | |
| JP5040195B2 (ja) | 反応性芳香族スルホン酸塩及びその製造方法 | |
| JP3981894B2 (ja) | ４，６−ジアミノレゾルシノール及び／又はその塩の製造方法 | |
| EP3950680A1 (de) | Verfahren zur herstellung von 3-hydroxyadipinsäure-3,6-lacton | |
| EP1673331A1 (de) | Verfahren zur rückgewinnung von dihydroxybiarylverbindungen | |
| JPS61259760A (ja) | 触媒の回収方法 | |
| JPH07247260A (ja) | スルホイソフタル酸誘導体の製造方法 | |
| JP2003335748A (ja) | 芳香族シアノ化合物の分離方法 | |
| JPH0211569A (ja) | 高純度２−クロロ−６−メチルアミノピリジンの製造方法 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM4A | Annulment or lapse of patent due to non-payment of fees |